Asymmetric Organocatalytic Michael/Henry Domino Reactions through Hydrogen-Bond Activation: Kinetic Access to Indane Scaffolds Bearing cis-Vicinal Substituents

Catalyst directs towards­ cis! A bifunctional hydrogen‐bond‐catalyzed Michael/Henry domino reaction allows preferential asymmetric access to the kinetic cis‐nitroindanol products with excellent enantioselectivity through a postulated matched transition state (see scheme; H‐Bo = hydrogen bond activat...

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Veröffentlicht in:Chemistry : a European journal 2013-08, Vol.19 (33), p.10822-10826
Hauptverfasser: Loh, Charles C. J., Atodiresei, Iuliana, Enders, Dieter
Format: Artikel
Sprache:eng
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Zusammenfassung:Catalyst directs towards­ cis! A bifunctional hydrogen‐bond‐catalyzed Michael/Henry domino reaction allows preferential asymmetric access to the kinetic cis‐nitroindanol products with excellent enantioselectivity through a postulated matched transition state (see scheme; H‐Bo = hydrogen bond activation). This high yielding protocol opens up a new strategy to access highly useful enantio‐enriched cis‐aminoindanol‐containing ligands and catalysts.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201302131